I am using IIS8.5 Windows Server 2012. When I replace the image in the source directory, why isn't the last modified triggered so that the client side is given the signal to repick the image from the server rather than its cache
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Because IIS have set the "Cache-Control Header" on static content to cache resource like images on browser for some days (at least).
See how Cache-Control header is set on IIS
Some Comments.
1. Don't change that static files cache but...
2. When you develop a site, press shift+reload to see the changes.
3. If you need to make update on the live site, either change the name of your image, either add some non used parameter at the end. (like image.jpg?r=111)
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